I was looking for someone to run with. He was looking for someone to drink with.

Random, but I went on a date last night.

Saturday I was bummed, I finally had some time to chill and was basically smacked in the face with the fact that most my friends royally suck these days. OK, that isn’t nice. True… but still not nice. Where did all my awesome friends go? (Answer: Boston, Copenhagen, Asshole-land, Boyfriend-ville…). After a good cry into my pillow (my go-to when it comes to tears), I finally had formulated what I was upset about. I want people in my life that take initiative – initiative to do things, initiative to have fun, initiative to not wait for someone else to make the plans. I wasn’t looking for a wild and crazy night, unless you consider renting movies and eating popcorn too much to handle. Of the various excuses, one took home the prize: “I went to the eye doctor this morning (approximately 10 hours prior to movie time) and had my eyes dilated so I think I want to stay close to home.” WTF?! I’m not asking you to read the NYT to me under bright lights or something. And I live 10 freaking blocks away. Whatever.

I decided to take matters into my own hands and find some new fun friends with initiative. Via Craigslist. Yeah, that could be trouble. Sticking to the “Strictly Platonic” section, I sought out females (between the ages of 28 and 33) looking for other females to hang out with. I came across one post that sounded promising and sent a cheerful email her way. Not finding much else out there in the way of new BFFs, I headed over to “Men Seeking Women,” mainly in search of a laugh.

Between

“Looking for a pantyhose lover to hang out with. C'mon. I'm a cool guy, and normal, too. Just looking for a woman that likes to wear pantyhose. I enjoy looking at women that wear pantyhose. There's gotta be a match out there somewhere, right?”

and

“Anyone want to make out today? I'm off, so anytime is fine. Not looking for more than cuddling up and kissing for a while. Age not important, you need to host, or be up for meeting somewhere. Lets trade pics and get kissing soon... “

I actually found a guy that sounded pretty good on paper.

Smart/dorky? Check.
Active? Check.
Confident? Check.
Good looking? Check.

Initiative? Man, I hope so.

He wanted to grab a drink that night, but I was in my pjs, drinking a bottle, err glass, of wine, getting ready to watch a cheesy romantic comedy with my roomie. But I took the plunge, sending him an email (with pictures attached) saying I had plans for the evening, but would be interested in a drink some other time.

So there we were – Sunday evening, enjoying one of my favorite happy hours, sitting at a table with a killer view overlooking the water. Three hours of conversation flew by and all expectations were exceeded. We said goodbye in the parking lot, both saying we’d have to do it again once I finished up with my finals and got back from conference in Oregon. I meant it. I thought he did too.

I drove home with a smile. Thinking about what it would be like to kiss him.

But then the girl in me started to analyze.

#1 We split the bill. Call me old-fashion, but I like it when the guy pays, especially when on a first date (I mean it was a date, right?). Even when dating someone, I’m much more a fan of – you pay this time, I’ll pay next time – it makes it feel more, I don’t know, special? This is a tough one to call – did he want to give off the vibe that he wasn’t feeling it? Is he cheap? Did he not want to offend me in case I was a feminist or something?

#2 The goodbye wasn't totally natural. I don’t know what I would have wanted – a kiss would have been overkill and I don’t do hugs (but he doesn’t know that). He did however put his hand on my shoulder when making a point about something moments before we parted ways. Hmmm… good right?

#3 He hasn’t emailed today to say he had a good time. I think I said I’d get in touch with him when I am back in town, but that doesn’t mean he can’t initiate contact before that, right? I feel like I have been bombarded with the idea that if a guy really likes you or wants to see you again, he is going to make a point to let you know. That the 3 day rule is so passé. In the past I’d have no problem sending him an email saying that I had fun and was looking forward to seeing him again, but after being completely unaware of how my last boyfriend truly felt about our relationship, I’m really going to need some positive, blatant reinforcement in the next relationship.

#4 He said in his post that he “would be thrilled if there was a spark,” but was also content to just make friends outside of his current circle. I said I wasn’t looking too hard for a new relationship, but wasn’t not looking either. How do I know if he thinks there is potential for the spark, or if he has already ruled it out?

#5 He might be too “water” and I might be too “mountains.” I’m getting way ahead of myself here (unconscious sabotage anyone?) but his job requires him to be near the ocean. My personal requirement for a future job is easy access to the mountains. He loves to surf like I love to ski. But maybe I should wait for Date #2 to worry about this one, huh?

So what do you guys think? I’m hesitant to talk about this with any of my (non-internet based) friends because then it becomes a little more real. I’ve been holding on to my past relationship as a defense mechanism to prevent me from getting hurt again, and while I know I need to move on – I’m scared. Scared, but hopeful.

I just need to chill, right?

Oh – and the potential new BFF? No word from her (and her post is gone). It was like a 50 word email. Did I really come off that uncool in so few words?